Jim Gaffigan on the Craft of Comedy and His Bourbon Brand (November 2025)

Jim Gaffigan is a stand-up comedian, bestselling author, and actor whose eleven comedy specials and widely shared bits have made him one of the most recognizable voices in comedy. In this conversation from November 2025, Jim Gaffigan sits down with Willie Geist at the third-ever Sunday Sitdown Live to reflect on his path from a small town in Indiana to selling out arenas and starring in film and television. Plus, he opens up about how David Letterman helped jumpstart his career, the origin of Fathertime Bourbon, and how the creative process continues to motivate him. (Venue sponsored by City Winery.) Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.